Diels-Alder trapping of an o-dinitroso intermediate in the 1-oxide/3-oxide interconversion of a 2,1,3-benzoxadiazole derivative

被引:28
作者
Sebban, M
Goumont, R
Hallé, JC
Marrot, J
Terrier, F
机构
[1] Univ Versailles, Lab SIRCOB, UPRES A CNRS 8086, F-78035 Versailles, France
[2] Univ Versailles, Lab IREM, Inst Laboisier, CNRS C0173, F-78035 Versailles, France
关键词
D O I
10.1039/a902170a
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
Convincing evidence is presented that the o-dinitroso intermediate involved in the exchange of the 1-oxide and 3-oxide tautomers of 6-nitro[2,1,3]oxadiazolo[4,5-b] pyridine 1-oxide 5 is the precursor of the Diels-Alder diadduct 7 isolated upon treatment of this compound with cyclohexadiene in CHCl3.
引用
收藏
页码:1009 / 1010
页数:2
相关论文
共 28 条
[1]   C-13 NMR-SPECTRA OF BENZOFUROXAN AND RELATED COMPOUNDS [J].
ANET, FAL ;
YAVARI, I .
ORGANIC MAGNETIC RESONANCE, 1976, 8 (03) :158-160
[2]  
[Anonymous], 1991, NUCLEOPHILIC AROMATI
[3]   REACTIONS OF FUROXANS WITH PHOSPHORUS YLIDES [J].
ARGYROPOULOS, NG ;
GALLOS, JK ;
NICOLAIDES, DN .
TETRAHEDRON, 1986, 42 (13) :3631-3636
[4]  
BOGER DL, 1987, HETERO DIELS ALDER M, P71
[5]  
BULACINSKI AB, 1975, TETRAHEDRON LETT, P3577
[6]   Ambident reactivity of aryloxide ions towards the super-electrophile, 4,6-dinitrobenzofuroxan. Kinetics, thermodynamics and stereoelectronic factors on regioselectivity [J].
Buncel, E ;
Manderville, RA ;
Dust, JM .
JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 2, 1997, (05) :1019-1026
[7]  
CRAMPTON MR, 1999, IN PRESS CAN J CHEM, P77
[8]   1,2-DINITROSOBENZENE IN ARGON MATRICES AT 14-K [J].
DUNKIN, IR ;
LYNCH, MA ;
BOULTON, AJ ;
HENDERSON, N .
JOURNAL OF THE CHEMICAL SOCIETY-CHEMICAL COMMUNICATIONS, 1991, (17) :1178-1179
[9]  
Evgen'ev MI, 1998, J ANAL CHEM+, V53, P571
[10]  
GALLOS JK, 1994, HETEROCYCLES, V37, P193